3-bromo-[1,1′-biphenyl]-2-amine | CAS 1620885-59-7

PRODUCT OVERVIEW

3-bromo-[1,1′-biphenyl]-2-amine | CAS 1620885-59-7  is a halogenated aromatic amine featuring a bromine substituent and a biphenyl core with an ortho‑positioned primary amine. This compound belongs to the class of aryl amines and is structurally characterized by a biphenyl scaffold, a motif widely leveraged in organic synthesis, medicinal chemistry, and materials science.

As a high‑value intermediate, 3‑bromo‑[1,1′‑biphenyl]‑2‑amine is used in cross‑coupling reactions, heterocycle formation, and diversification chemistries. The presence of both a bromide leaving group and a nucleophilic amine in close proximity offers unique reactivity that enables construction of complex molecules for research and development applications.

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CHEMICAL IDENTITY

• Name: 3‑Bromo‑[1,1′‑biphenyl]‑2‑amine

• CAS Number: 1620885‑59‑7

• Molecular Formula: C₁₂H₁₀BrN

• Molecular Weight: 248.12 g/mol

• Synonyms:

  • 2‑Amino‑3‑bromobiphenyl

  • o‑Aminophenyl(3‑bromophenyl)

This compound’s structure consists of two phenyl rings joined at carbon‑1 positions, with a bromine atom at the 3‑position of one ring and a primary amine at the 2‑position of the other. These functional groups impart distinct electronic properties and enable selective transformations under appropriate reaction conditions.

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PHYSICAL AND CHEMICAL PROPERTIES

3‑Bromo‑[1,1′‑biphenyl]‑2‑amine is typically encountered as a solid crystalline material at ambient conditions. Its physicochemical characteristics include:

• A bromine substituent that increases molecular weight and contributes to relatively higher density among monofunctional biphenyl derivatives.

• A primary amine that can participate in acid‑base chemistry, forming salts with acids and facilitating diverse downstream chemistry.

• Aromaticity that provides thermal stability and makes the compound compatible with a range of synthetic transformations.

Because of the electron‑withdrawing influence of the bromine atom in conjunction with the electron‑donating amine group, this compound exhibits differential reactivity across its aromatic rings, making it an excellent candidate for regioselective coupling reactions.

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SYNTHETIC APPLICATIONS & CHEMISTRY

The dual functionalization of 3‑bromo‑[1,1′‑biphenyl]‑2‑amine—bearing both a halide leaving group and a nucleophilic amine—makes it a versatile intermediate in modern organic synthesis. Key applications include:

Cross‑Coupling Chemistry

The aryl bromide moiety readily participates in palladium‑catalyzed cross‑coupling reactions such as:

• Suzuki‑Miyaura coupling

• Buchwald–Hartwig amination

• Negishi or Stille coupling

These reactions enable the installation of varied substituents and extended π‑systems, tailoring properties for target molecules in pharmaceuticals and materials chemistry.

Heterocycle Construction

The proximity of the amine and aryl halide offers efficient entry into heterocyclic systems. For example:

• Cyclization to nitrogen‑containing heterocycles such as indoles, benzazepines, and quinolines.

• Useful in medicinal chemistry for generation of bioactive scaffolds.

Amide and Urea Formation

The primary amine can be transformed to amides, carbamates, or ureas through reactions with acyl chlorides, isocyanates, or activated esters. This functional group versatility enables:

• Linker attachment in drug conjugates

• Modification for material properties

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MEDICINAL CHEMISTRY & RESEARCH UTILITY

In drug discovery and pharmaceutical research, 3‑bromo‑[1,1′‑biphenyl]‑2‑amine plays a role as an intermediate building block for lead compounds and analog libraries. Its inclusion in synthetic routes supports:

• Scaffold hopping

• Structure‑activity relationship (SAR) studies

• Generation of diversified compound libraries

The biphenyl moiety is a common structural feature in many drugs and candidates due to its planar topology and ability to engage in π‑π interactions with biological targets. By providing a functionally adaptable intermediate, this compound aids researchers in rapidly exploring chemical space.

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ANALYTICAL CHARACTERIZATION

High‑purity samples of 3‑bromo‑[1,1′‑biphenyl]‑2‑amine are characterized using standard analytical techniques:

• Nuclear Magnetic Resonance (NMR) Spectroscopy — Confirms chemical structure, substitution pattern, and purity.

• Mass Spectrometry (MS) — Verifies molecular weight and fragmentation profile consistent with the bromo‑biphenyl amine architecture.

• High‑Performance Liquid Chromatography (HPLC) — Assesses purity and identifies trace impurities.

• Infrared (IR) Spectroscopy — Detects characteristic functional group vibrations (e.g., amine N–H stretches).

These analytical methods ensure the compound meets rigorous quality criteria for use in research and development applications.

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SAFETY & HANDLING GUIDELINES

3‑Bromo‑[1,1′‑biphenyl]‑2‑amine should be handled with care in a well‑equipped laboratory. Key considerations include:

• Personal Protective Equipment (PPE): Use appropriate gloves, lab coat, and eye protection.

• Ventilation: Conduct manipulations in a fume hood to minimize inhalation exposure.

• Storage: Keep container tightly closed, away from strong oxidizers or bases.

• Reactivity: The amine group can react with strong acids and acylating agents; the aryl bromide can undergo coupling under catalytic conditions.

Comprehensive Safety Data Sheets (SDS) are available to guide proper handling, disposal considerations, and emergency procedures.

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CONCLUSION

3-bromo-[1,1′-biphenyl]-2-amine | CAS 1620885-59-7  is a structurally versatile and highly functional intermediate designed to support advanced organic synthesis, medicinal chemistry, and materials science research. Its combination of a reactive halogen and nucleophilic amine in a biphenyl framework enables myriad chemical transformations. With rigorous analytical characterization and robust safety documentation, it is positioned as a reliable reagent for discovery and development workflows.